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Preface | |
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To the Student | |
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To the Instructor | |
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Acknowledgments | |
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The Structures of Organic Molecules | |
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Structural Components of Organic Molecules | |
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Structural Formulas and Condensed Structures | |
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Systematic Nomenclature: IUPAC Names | |
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Constitutional Isomers and Hydrocarbon Substituents | |
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Naming Organic Compounds | |
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Chapter Summary | |
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Bonding in Organic Molecules | |
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Lewis Structures | |
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Bond Properties | |
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Resonance Structures | |
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The Formation of Bonds | |
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Hybrid Orbitals and Shapes of Molecules | |
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Bonus with Herteroatoms | |
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Delocauzed 71 Electron Systems | |
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Noncovalent Interactions | |
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Chapter Summary | |
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The Conformations of Organic Molecules | |
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Conformations of Acyclic Compounds | |
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Conformations of Cyclic Compounds | |
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Conformations of Substituted Cyclohexanes | |
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Conformations of Other Cyclic Compounds | |
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Chapter Summary | |
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The Stereochemistry of Organic Molecules | |
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Geometric Isomers of Alkenes | |
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Chirality and Enantiomers | |
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Diastereomers | |
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Fischer Projections | |
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Reaction Stereochemistry: A Preview | |
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Chapter Summary | |
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Chemical Reactions and Mechanisms | |
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General Aspects of Reactions | |
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Acid-Base Reactions | |
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Reaction Mechanisms | |
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Reaction Coordinate Diagrams | |
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Reactions in Biological Systems | |
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Chapter Summary | |
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Substitution Reactions of Alkyl Halides | |
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Fundamental Aspects of Substitution Reactions | |
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The SN1 Reaction of Alkyl Halides | |
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The SN2 Reaction of Alkyl Halides | |
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A Comparison of the SN1 and SN2 Mechanisms | |
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Chapter Summary | |
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Substitution Reactions of Alcohols and Related Compounds | |
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Substitution Reactions of Alcohols | |
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Substitution Reactions of Ethers and Epoxides | |
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Substitution Reactions of Thiols and Thioethers | |
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Substitution Reactions in Biochemical Systems | |
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Chapter Summary | |
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Elimination Reactions of Alkyl Halides, Alcohols, and Related Compounds | |
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The E1 Reaction | |
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The E2 Reaction | |
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Substitution Versus Elimination | |
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Elimination Reactions in Biology | |
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Chapter Summary | |
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Addition Reactions of Alkenes and Alkynes | |
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Electrophilic Addition Reactions of Alkenes | |
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Electrophilic Addition Reactions of Alkynes | |
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The Formation of Carbon-Carbon Bonds | |
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Hydroboration Reactions of [Pi] Bonds | |
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The Addition of Carbenes to [Pi] Bonds | |
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Chapter Summary | |
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Addition Reactions of Conjugated Dienes | |
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The Structures of Dienes | |
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Bonding in Conjugated Dienes | |
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Electrophilic Addition to Conjugated Dienes | |
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The Diels-Alder Reaction | |
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Chapter Summary | |
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Oxidation and Reduction Reactions | |
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Oxidation States in Organic Molecules | |
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Hydrogenation Reactions | |
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Oxidation Reactions of Alkenes | |
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Oxidation Reactions of Alcohols | |
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Oxidation Reactions of Amines | |
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Chapter Summary | |
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Free Radical Reactions | |
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Free Radical Halogenation Reactions | |
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Reduction via Radical Intermediates | |
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Free Radical Addition Reactions | |
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Oxidation via Radical Intermediates | |
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Chapter Summary | |
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Proton and Carbon NMR Spectroscopy | |
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Chemical Shifts and Proton Equivalence | |
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Spin Coupling in Simple Systems | |
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Interpreting and Predicting 1h NMR Spectra | |
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Spin Coupling in More Complex Systems | |
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Carbon NMR Spectra | |
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Interpreting 13C NMR Spectra | |
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Chapter Summary | |
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Determining the Structures of Organic Molecules | |
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Analytical Data in Structure Determinations | |
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Mass Spectrometry | |
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Infrared Spectroscopy | |
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Combined Structure Determination Exercises | |
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Chapter Summary | |
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Organometallic Reagents and Chemical Synthesis | |
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Carbon-Carbon Bond Formation | |
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Organomagnesium and Lithium Compounds | |
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Transition Metal Organometallic Compounds | |
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Retrosynthesis | |
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Selectivity Criteria in Synthesis | |
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Chapter Summary | |
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Asymmetric Reactions and Synthesis | |
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Chiral Compounds | |
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Enantiomeric Resolution | |
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Asymmetric Synthesis | |
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Enantioselective Addition Reactions | |
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Synthetic Design of Chiral Molecules | |
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Chapter Summary | |
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The Chemistry of Benzene and Its Derivatives | |
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Structural Aspects of Aromatic Molecules | |
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Electrophilic Substitution Reactions of Benzene | |
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Electrophilic Substitution Reactions of Benzene Derivatives | |
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Other Reactions of Benzene and Its Derivatives | |
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Chapter Summary | |
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Nucleophilic Addition Reactions of Aldehydes and Ketones | |
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General Aspects of Nucleophilic Addition Reactions | |
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Nucleophilic Addition Reactions | |
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Reduction Reactions of Aldehydes and Ketones | |
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Oxidation Reactions of Aldehydes and Ketones | |
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Chapter Summary | |
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Addition-Substitution Reactions of Aldehydes and Ketones: Carbohydrate Chemistry | |
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Hemiacetals and Acetals | |
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Acetals as Protecting Groups | |
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Carbohydrates | |
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Glycosides | |
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Oxidation and Reduction Reactions of Carbohydrates | |
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Chapter Summary | |
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Addition-Elimination Reactions of Aldehydes and Ketones | |
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Compounds with Carbon-Nitrogen Double Bonds | |
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Imine Chemistry and Biochemistry | |
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Enamines | |
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Ylides | |
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Chapter Summary | |
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Addition-Elimination Reactions of Carboxylic Acids and Derivatives | |
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General Aspects of Structure and Reactivity | |
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Reactions of Carboxylic Acids | |
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The Chemistry of Acid Chlorides, Thioesters, and Anhydrides | |
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The Chemistry of Esters | |
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The Chemistry of Amides | |
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The Chemistry of Nitriles | |
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Reactions with Organometallic Compounds | |
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Reduction Reactions of Carboxylic Acids and Derivatives | |
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Chapter Summary | |
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The Acid-Base Chemistry of Carbonyl Compounds | |
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Acidity of Carbonyl Compounds | |
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Enols and Enolate Ions | |
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Reactions of Enolate Ions | |
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Dicarbonyl Compounds | |
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Reactions of Amide and Imide Ions | |
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Chapter Summary | |
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The Nucleophilic Addition Reactions of Enolate Ions | |
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The Aldol Reaction | |
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Crossed-Aldol Reactions | |
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The Claisen Condensation | |
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Crossed-Claisen Condensations | |
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Chapter Summary | |
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Conjugate Addition Reactions of Unsaturated Carbonyl Compounds | |
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[alpha],[Beta]-Unsaturated Carbonyl Compounds | |
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Conjugate Addition Reactions | |
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Conjugate Addition Reactions of Carbanions | |
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Reduction Reactions | |
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Chapter Summary | |
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The Chemistry of Polycyclic and Heterocyclic Arenes | |
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Polycyclic Aromatic Compounds | |
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Pyridine and Related Heterocycles | |
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Pyrrole and Related Heterocycles | |
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Azoles | |
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Chapter Summary | |
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Polymers and Polymerization | |
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Polymers and Their Properties | |
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Chain-Growth Polymerization | |
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Step-Growth Polymerization | |
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Modification of Polymers | |
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Chapter Summary | |
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Amino Acids, Peptides, and Proteins | |
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Amino Acids | |
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Chemical Synthesis of Amino Acids | |
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Asymmetric Synthesis of Amino Acids | |
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Peptide Synthesis and Analysis | |
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Protein Structures | |
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Chapter Summary | |
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Nucleic Acids and Molecular Recognition | |
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Nucleosides and Nucleotides | |
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Nucleic Acid Structures | |
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Molecular Recognition | |
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Crown Ethers and Cryptands | |
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Cavity-Containing Molecules | |
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Recognition Using Hydrogen Bonds | |
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Chapter Summary | |
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Appendix | |
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Glossary | |
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Index | |